Azo dyestuffs insoluble in water and process of making same



Patented dune 1?, i924.

unis sets ARTHUR ZITSCHER AND AUGUST LEOPOLD LAS FOFFENlBACH-ON-THE-MAIN,

GE, ASSIG-NORS T0 FORT-ON-THE-MAIN, GE 2". 11m- AZO DYEST'UFFS INSGLUBLEIN WATER AND PBQCESS 9F Ho Drawing.

T 0 all whom it may concern:

Be it known'that we, ARTHUR ZITSCHER and AUGUST Lnorono LASKA, bothcitizens of the German Republic, and residents of Ofienbach-on-the-Main,Germany, have invented certain new and useful Improvewherein R means anot sulfonated arylresidue not containing an auxochromic group, n anumber bein atleest 1. The dyestuiis can be obtained by combinin adiazotized not sul'foneted aminoazobo y, derived from diazocompounds notcontaining an auxochromic group and aminoderivatives of monoorpolyvalent phenolalkylethers, with an arylid oi 2.3-oxynaphthoic acid.The dyestutls are when dry maroon to black powders, insoluble in water,soluble in sulfuric acid to e. bluish g" to violet solution, yieldingupon reducton with an auxochromic group such as of anilin, its homoloues and substitution products, such as toluidm, Xyhdm.an1s1d1n,cres1d1n,chloroand nitroa-nilins, chloroand nitrotoluidins,chloroand nitroxylidins, choloand nitroanisidins, chloroandnitrocresidins, czand {l-naphthylamin or their derivatives such asaminonaphtholether, aminomethylnaphthalene. chloroor nitronaphthylagminsand others, with for instance an aminocresolalkylether,ecetylaminoanisidin or aminohydroquinonedielkylether.

As azocomp'onents we may use all the arylids of 2.3-onynapthoic acid,such as the anilid, toluidids, anisidids, phenetidids, m-

and (5-naphthelids, 2.3-oxynephthoylnminothiazol. -me;ta-toluyleneend-pera-pheny we FABEIK emmnn lift-'1 nn'rnon, or

.NG- SE.

Application filed July 8, 1923. Serial No. 649,3fi8.

ments in Azo Dyestuds Insoluble in Water and Processes of Making Same,of which the following is a specification.

Our invention relates to new dyestuffs having probably the generalformula:

endiamin, arylids, chloroor nitrosubsti tuted, and the like.

The following examples illustrate the invention, the parts being byweight;

Example 1. A diazosolution, preparedwith 30,7 arts of the aminoazobody,derived from d1azotized oz -naphthylamin and aminohydroquinonedimethylether, is combined with a solu-.

tion of 27,6 parts of the anilid of 2.3- oxynaphthoic acid in dilutecaustic soda lye, with the addition of an excess of sodium acetate andTurkey red oil. The se aratcd dyestud is filtered and washed. or theproduction of color lelres it may be used advantageously in form of apaste. The lakes, prepared therefrom in the usual manner,

give darkly bluish black glue-watercolors of u very good fastness.Production of the dyestuds on the fiber.

Example 2.

I. The yarn, having been well boiled and dried, is impregnated with asolution of gr. of az-naphthalid of 2.3-oxynaphthoic acid, 1

c. c. of caustic soda lye of 34 Be. and c. c. of Turkey red oil in theliter, well wrun' out and without being dried developed Hi adiezosolution, containing sodium acetate end 6 gr. of the eminoazoloody,derived from diazotized c-naphthylamin and para-cresidin oraminohydroquinonedimethylether or derived from fi-naphthylamin andaminohydro uinonedimethylether in the liter.

In t is manner we obtain reddish black tints with the eminoazobody,derived from diezotized cz-nephthylamin and para-cresidin, bluish blacktints with the body de rived .from diazotized cand d-naphthyl: swim andaminohydroquinonedimethylether, ell tints being of a. very goodia'stness,

ill)

' and an arylid of 1-amino-2-oxy-3-naphthoic Now what we claim anddesire to secure by Letters Patent, is the 'following:

1. As new articles the azodyestufi's, in-

soluble in water, having probably the gen-' eral forrrula: 5

wherein R means a not sulfonated "arylresidue not containing anauxochromic group, n a number being at least 1, said dyestufi being,when dry, maroon to black wders, insoluble in water, soluble in sul-' ouric acid to a bluish green to violet solution, yielding upon reductionwith stannous' chloride an arylamin, a derivative of diamino-benzenecontaining atleast one O-alkylgroup and an arylid of l-amino-Q-oxy-3-naphthoic acid, said dyestufls being useful for the production ofvaluable pigment colors and giving, when produced on the fiber, maroonto black shades of an excellent fastness to washing and chlorine.

wherein R means a not sulfonated arylresidue not containing anauxochromic group X a monovalent atom or cup ex.- cept l1, saiddyestufis being, w en dry, maroon to black powders, insoluble in water,soluble in sulfuric acid to a bluish een to violet solution, yieldingupon reductlon with stannous chloride an arylamin, a derivative ofpara-diaminobenzene, containing an O- alkylgroup in ortho-position tothe one am nogroup, a monovalent atom or group in ortho-position to theother aminogroup,

acid, said dyestuffs being useful for the production of valuable pigmentcolors and giving, when produced on the fiber, maroon to black shades ofanexcellent fastness to washing and chlorine.

5. A soluble 1n water, consisting incombining diazotized not sulfonatedaminoazobodies 0-Alkyl I rocess of making azodyestufl's, in-

I A I-NEoo- I l a W from diazocompounds not containing an auxochromicgroup and bodies of the general formula:

0-Alkyl X meaning a lnonovalent atom or group except H, with arylids of2.3-oxynapl1thoic acid.

6. Textile materials dyed with one of the dyestuffs covered by claim 4,said dyestufi being developed on the material.

7. As new articles the azodyestufi's, insoluble in water, havingprobably the general formula: V

I I Mm ar l-Nnook wherein R means a not sulfonated aryllresidue, notcontaining an auxochromic grou j, said dyestuffs being, when dry, black80 pow ers, insoluble in water, soluble in' sulfuric acid to a bluishgreen to violet solution, yielding upon reduction with stannous chloridean arylamin, a 2.5-diaminohydroquinonedialkylether and an arylid of, 1-

mean 117 amin0-2-0Xy-3-naphthoic acid, said dyes stuffs being useful forthe production of valuable pigment colors and giving, when produced onthe fiber, black. shades of an 5 excellent fastness to washing andchlorine.

8. A process of making azodyestufis, insoluble in Water, consisting incombining diazotized not sulfonated aminoazobodies from diazocompoundsnot containing an 0 auxoehromic group and aminohydroquinonediallqlethernaphthoic acid.

, .with arylids of 2.3 oxy- 9. Textile materials dyed with one of thedyestuiis covered by claim 7, said dyestuff bein developed on thematerial.

In testimony, that We claim the foregoing as our invention, We havesigned our names, this 14th day of June, 1923.

AUGUST minnow mam. [1b. a] ARTHUR znrscnnza. [n a] Witnesses PETERLAUTENSOHLAGER, FRIEDRIGH Dnson.

